The Portland Cheat Sheet
Everything Free 7 Days a Week in Greater Portland, Maine
The tradition of chalk art on pavement began in 16th century Italy where drifting artists traveled between festivals living off coins thrown by their drawings. Today there are between 50 to 100 chalk festivals in the U.S. annually, including this weekend's street fair in Kennebunkport, Sept 23-24. Here's the schedule and slideshows from 2017, 2018 & 2019 to pique your curiosity.
Text: Town of Kennebunkport's "Chalk Art History" (watch the free documentary) Image: Carol Cook and Katahdin
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Thursday, September 22
Free Moose Hunting Trip for a Purple Heart Vet (Sept 24-Oct 2)
Give Input to Improve Regional Transit, 8 am-4 pm, 3 Locations, Portland
Craft & Chat for Ages 50+ (weekly), 9-11 am, Community Ctr., South Portland
Age-Friendly Guided Walk, 10 am, Simpson's Woods, Freeport
Watch the Maine Senior Games- Candlepin Bowling, 10 am, Big 20, Scarborough
Local Hikes for Ages 50+, 10 am-12 pm, Falmouth
Farmington Fair $5 Admission Ages 62+, 12-7 pm, Farmington
Walk with a Doc, 12:15-12:45 pm, Wellness Wy., Topsham
People Plus Open House, 1-3 pm, Union St., Brunswick
Theater: Sun Universe, 2-2:45 pm, School St., Brunswick
Artist talk: Paula Gerstenblatt, 2-4 pm, Jewish Museum, Portland
Senior College- Aging, Health & Happiness, 2-4 pm, Library, Auburn
Whiskey Worth Knowing & Engraving (tasting), 4-6 pm, Man & Oak, Portland
Talk & Reception: Thinking about Migration through Latinx Art, 4:30-7 pm, Bowdoin, Brunswick
Wine Tasting, 5-7 pm, Vessel & Vine, Brunswick
BIPOC Business After Hours, 5:30-7:30 pm, Washington Ave., Portland
Community Spokes Bicycle Advocate Training, 5:30-7:30 pm, Portland
Meetup, Active Singles 40-60s- Trivia Night, 5:30-7:30 pm, Flight Deck, Brunswick
BYO Crafts Senior Drop In (Th weekly), 5:30-8 pm, Senior Ctr., Auburn
Monthly Dinner for Older LGBTQ+ Adults ($0-8), 6 pm, Portland
City Climate Action Plan Public Workshop, 6:30 pm, Town Hall, Falmouth
Movie: Running Home (doc), 6:30 pm, The Point, South Portland
Teen Game Night, 6:30-8 pm, Library, Cumberland
The Playful Process of Song Making Workshop ($0+), 6:30-8:30 pm, Greenwood Garden, Peaks Island
Movie: Belfast, 6:45-8:30 pm, Library, Kennebunkport
Bike Bidd/Saco Lights & Music Bike Ride, 7-9 pm, Main St., Biddeford
Outdoor movie: Wreck-It Ralph, 7-9 pm, Nonantum, Kennebunkport
Outdoor movie: Outdoor Film Festival Shorts ($0-10), 7 pm, Pearl St. Garage, Biddeford
Virtual Events
Funding Your Business, 12 pm
Freezing Fruits & Vegetables, 12-12:45 pm
Preserving the Maine Harvest Workshop ($0-5), 12-12:45 pm
Holiday Prep- Social Media Marketing, 12-1 pm
Credit Score Improvement Seminar, 5:30-6 pm
Join the Youth Voting Network, 5:30-6:30 pm
Leveraging Your Power with the Maine Women's Lobby, 6-7:30 pm
Stars Over Katahdin 2022- Astronomy Talks, 6:30-8 pm
Meetup, Acoustic Guitar Jam, 6:30-8:30 pm
Meditation with Melissa Boyd (hybrid; $0+), 7 pm
Friday, September 23
Common Ground Fair Free for Disabled, Under 12 & Volunteers (9/23-25), Unity
$3 Furniture Fridays at Goodwill (ends Sept 30)
Overdose Recognition, Narcan & CPR Training, 7:30-8:30 am, Vets Center, Windham
Free Book & Puzzle Swap (M-F all year), 8 am-4:30 pm, Town Hall, Kennebunk
Maine State Championships All Breed Horse Show (9/23-25), 8 am-night, Fairgrounds, Skowhegan
Crop Cover Volunteer Day, 9-11 am, Hacker's Hill, Casco
Volunteer Work Day at Tear Cap Workshops, 9-12 pm & 1-4 pm, Hiram
Chalk the Port, 9 am-4 pm, Recreation Way, Kennebunkport
Games & Gather for Ages 55+ (Tu,F weekly), 10 am-2 pm, Hub, Scarborough
Meetup, Maine Women in Tech, 10 am-2 pm, Rwanda Bean, Portland
Animal Ambassador Visit, 12-2 pm, Maine Beer Co., Freeport
Bio365 Biochar Soil Launch + Swag, 12-4 pm, HTG Supply, Portland
Northpoint Mortgage Ribbon Cutting + Food, 12-4 pm, Rt. 1, Falmouth
Music: New Relm, 2 & 7 pm, Sawyer Rd., Greene
Author talk: Memoirs of an Amish Childhood, 2-3:30 pm, Library, Lewiston
LGBTQIA + Allies Teen Hangout, 2:30-4 pm, Library, Cumberland
Champlain French Film Festival, 4 pm, USM, Portland
Community Yoga Class ($0+), 4:30-5:30 pm, The Daily Sweat, Kennebunk
CornerFEST, 4:30-7:30 pm, Woodford St., Portland
Queer Makers Night Market, 5-9 pm, Congress Sq. Park, Portland
Youth Advisory Board Meeting (ages 11-13), 5:30 pm, Hub, Scarborough
Variety Open Mic Coffee House, 6 pm, River Rd., Windham
Reiki Session, 6-7 pm, Library, Raymond
Trails in the Valley Run Club (weekly), 6-7 pm, Lost Valley, Auburn
Music: Concert for Huot House Homeless Vets ($0-5), 6-8 pm, Grange 53, Saco
21+ Karaoke Night, 6-10 pm, Roosevelt Trl., Windham
Dempsey Challenge's "A Night of Love + Light", 6:30-8 pm, Simard-Payne Park, Lewiston
Music: Genticorum ($0-20), 6:30-8 pm, Church Ave., Peaks Island
Music: BasementBangerz (ages 16+), 7-10 pm, Main St., Sanford
Music: 4 Bands, "A Night of Horrific Noise" ($0-10), 8 pm, Apohadion, Portland
Saturday, September 24
Free Admission to All National Parks
12 Farmers' Markets Today> Here's the Weekly Schedule
Marsh Bird Walk, 8-9:30 am, Blue Point Preserve, Scarborough
Document Shredding + Canned Food Drive, 8 am-12 pm, Saco & Bidd Savings, Biddeford
Nerdcamp Literary Un-Conference, 8 am-3:30 pm, USM, Gorham
Scent Work AKC Dog Show, 8 am-6 pm, Robie School, Gorham
Chalk the Port + Live Music, 8 am-7 pm, Recreation Way, Kennebunkport
Maine State Championships All Breed Horse Show, 8 am-night, Fairgrounds, Skowhegan
September Volunteer Work Party, 9-11 am, Turkey Hill Farm, Cape Elizabeth
Last of Season Makers Market, 9 am-4 pm, Ossipee Trl, Standish
Kids Bike Ride Race (ages 5-12), 9:15 am, Arundel
Champlain French Film Festival, 10 am, 2, 4, 6 pm, USM, Portland
Clark's Pond Trail Ribbon Cutting, 10-10:30 am, South Portland
Fall Trail Clean Up Day, 10 am-12 pm, Clifford Park, Biddeford
Urban Foraging with Rewild Maine, 10 am-12 pm, Town Hall Trailhead, Cumberland
Repair Cafe (repair items to reduce waste), 10 am-12:30 pm, Library, Brunswick
Mock SAT Exam, 10 am-1 pm, Library, Falmouth
Listen to/Join the All-Ages Drum & Bugle Corp, 10 am-2 pm, Broadway, South Portland
Pollinator Bioblitz, 10 am-2 pm, 3 parks, South Portland
Veterans & Family Outdoor Expo, 10 am-2 pm, Cabela's, Scarborough
23rd Apple Pumpkin Festival, 10 am-3 pm, Rec Fields, Livermore Falls
Harvest Fair- Petting Zoo, Kid Stuff, 10 am-3 pm, St. Brigid, Portland
Shaker Museum Apple Festival, 10 am-4 pm, Alfred
Mountain Bike Social & Group Ride ($0-20), 10:30 am, Industrial Wy., Portland
Kids Carnival (followed by free football game), 11 am-1 pm, Bates, Lewiston
Cahoots- Art, Community, Music, Free Pizza, 11 am-2 pm, McKeen St., Brunswick
Artisan Fair, 11 am-4 pm, Wallingford's Fruit House, Auburn
Fall Fest 2022, 11 am-4 pm, Veteran's Park, Old Orchard
Free Subs & Soda, 11:30 am, Big Moose Harley, Portland
American Shaman CBD Ribbon Cutting, 12-2 pm, Maine St., Brunswick
Outdoor music + Historical Grocery Open House, 12-3 pm, Windham Ctr. Rd., Windham
New Story Walk + Food, Lawn Games, 1-2 pm, Community Ctr., North Yarmouth
Clean Elections Sign Making Party + Cider, Donuts, 1-3 pm, Payson Park, Portland
Open Bench Project Space Tour, 1-3 pm, Congress St., Portland
Androscoggin Co. Fish & Game Open House, 1-4 pm, Perkins Ridge Rd., Auburn
Old Fashioned Games & Open House, 1-4 pm, Knight House, Auburn
Youth in Recovery Fall Field Games Day, 1-5 pm, Bishop St., Portland
Steven King Trivia Time, 1:30-2:30 pm, Library, Gray
Meetup, Portland by Night- Apple Picking, 2-4 pm, Randall Orchards, Standish
Self Defense Class for Immigrant Women, 3-5 pm, TBD, Portland
Mid-Autumn Moon Festival Potluck, 3-6 pm, Ft. Williams, Cape Elizabeth
Dimensions in Jazz Workshop, 4-5:30 pm, Neal St., Portland
September Frith Farm Tour ($0-20), 4-6 pm, Scarborough
Meetup, Russian Portland, 5-7 pm, Portland
Longfellow Park's 95th + Salsa Dancing, Music, 5-8:30 pm, Portland
Watch/Join Maine Mayhem Women's Football Tryouts, 5:30 pm, Ludlow St., Portland
Drum Circle ($0+), 6-7:30 pm, Flourish, Biddeford
Outdoor music: American Ride, 6-9 pm, Main St., Bridgton
Nautical Star Party with Maine's First Ship, 6-9 pm, Commercial St., Bath
Twilight in the Park- Luminarias for Deceased, 6:30 pm, Deering Oaks, Portland
Sunday, September 25
Cumberland Fair Free for Wheelchairs & Kids <12 (9/25-10/1), Cumberland
Maine State Championships All Breed Horse Show, 7:30 am-end, Fairgrounds, Skowhegan
Audubon Field Trip- Androscoggin River Trail, 8-11:30 am, Lisbon
Meetup, Join a 6-Man Rowboat Crew (weekly), 8:30-10 am, Lake Auburn, Auburn
Cars & Coffee, 9 am, MacDonald Motors, Bridgton
Free Photo Session with Kids/Adult Dresses, 9 am-2:45 pm, Ft. Williams, Cape Elizabeth
The Impact of Mindset, Mental Toughness & Attitude, 10-11 am, H2O Fitness, Scarborough
Matchless Firestarting & Campfire Safety, 10-11:30 am, Sheridan St., Portland
Electrify Freeport Clean Energy Expo, 10 am-2 pm, High School, Freeport
Shaker Museum Apple Festival, 10 am-4 pm, Alfred
Free Apple Picking for SMCC Family & Friends, 10 am-6 pm, Orchard Ridge, Gorham
Queer Makers Market, 11 am-3 pm, Congress Sq. Park, Portland
Artisan Fair, 11 am-4 pm, Wallingford's Fruit House, Auburn
Watch Medieval Knights Practice Fighting, 12 pm, W. Auburn Rd., Auburn
End of Season Car Show + Country Band, 12-5 pm, Bentley's, Arundel
Board Games at Historic Schoolhouse, 1-4 pm, Boothby St., Auburn
Hang with Infinite Kindness Project (nurse burnout), 2:30-4:30 pm, Chebeague Isl.
Author talk: Phuc Tran, Sigh Gone ($0+), 3 pm, Arts Center, Denmark
Music: Resonant Rogues, 3-5 pm, Maine Craft, Portland
Paws & Read with Therapy Dogs, 3:30-4:30 pm, Library, Freeport
Explore Tarbox Preserve, 4:30-6 pm, Topsham
Community Kirtan ($0-15), 6-7:30 pm, Flourish, Biddeford
Meetup, Book Lovers Reading & Literacy Group, 6-7:30 pm, Panera, South Portland
Outdoor movie: The General (silent), 6:30-8 pm, Congress Sq. Park, Portland
Monday, September 26
Cumberland Fair- $5 Day for Military/Vets; Homeschool/Day Care Free, 6 am-7 pm, Cumberland
Age-Friendly Yoga (weekly), 9:30 am, Community Ctr., Freeport
Seniors: The Nature of Fall, 10-11 am, Senior Ctr., South Portland
Amish Star Hot Pad Class, 10 am-12 pm, Community Ctr., Falmouth
Rosh Hashanah + Potluck, 10 am-1 pm, Main St., Ogunquit
Learn More About Medicare, 10:30-11:30 am, Library, Topsham
Cards for Ages 50+ (M,Th weekly), 12-3 pm, Community Ctr., South Portland
Let's Talk About Hospice, 1 pm, Library, Scarborough
Shofar in the Park (Rosh Hashanah), 4:30-5 pm, Ft. Allen, Portland
Talk: The Bifurcation of America, 5-7:30 pm, UNE, Portland
Yoga on the Hill, 5:30-6:30 pm, Hacker's Hill, Casco
Sign Language Class, 6-7 pm, Library, Windham
Hip Hop in the Park, 6-8 pm, Congress Sq. Park, Portland
Intro to Acting Class, 6-8 pm, call for location, Portland
Talking to Your Kids About Sex, 6-9 pm, Maine Mall Rd., South Portland
Talk: The Mystery of Maine's Wildlife, 7-8 pm, Library, Brunswick
Improv Comedy Incubator (weekly; $0-5), 7-9 pm, Woodfords Club, Portland
Tuesday, September 27
Meetup, HIIT Class, 6-6:45 am, Payson Park, Portland
Cumberland Fair- $5 Ages 65+ Today, 7 am-7 pm, Cumberland
L/A ‘Think Local’ Biz Networking (hybrid; weekly), 8:30 am, Lisbon St., Lewiston
Senior Finance- Budgeting & Inflation, 9-10 am, Senior Center, South Portland
Free Admission Tuesday (weekly), 10 am-5 pm, Brick Store Museum, Kennebunk
Walk with a Doc, 12:15-12:45 pm, Maine St., Brunswick
Teen Apple Printing, 3:30-4:30 pm, Library, Kennebunk
Kids Chess Club (weekly), 4-5 pm, Library, Cumberland
Business After Hours Networking, 5-7 pm, Blaze Brewing, Biddeford
Girl Scouts K-3 Sign Up & Activity, 5:30-6:30 pm, Mast Landing, Freeport
Wes McNair Open Air Book Launch, 6-7 pm, Congress Sq. Park, Portland
Ticks- A Proactive Approach, 6:30 pm, Library, Cumberland
Slow Flow New Moon Yoga ($0-20), 7-8 pm, Flourish, Biddeford
Virtual Events
Holiday Prep- How to Manage Shipping Costs, 10:30-11:30 am
End of Year Business Tax Planning, 2-3 pm
League of Women Voters Discussion Forum, 6:30-7:30 pm
Talk on Maine Wildlife, 6:30-7:30 pm
Book talk: History of America's Public Lands, 7-8 pm
How Maine’s Warming Winters Affect Our Forests, 7-8:30 pm
Wednesday, September 28
November Project- Maine State Pier Workout, 6:29 am, Portland
Local Business Networking, 8:15-9:45 am, Run of the Mill, Saco
Pondicherry Park Walk, 9-10 am, Bridgton
Bingocize (bingo + exercise; M,W weekly), 10-11 am, Republic Ave., Topsham
Cribbage ($3; weekly), 10 am-12 pm, Town Hall, Buxton
Voter Registration Day, 10 am-1 pm, Library, South Portland
Drop In Group for New Parents (weekly), 12:15-2 pm, Birth Roots, Portland
Get Out! Fungi Nature Walk, 1:30-3 pm, Sam Ristich Trails, North Yarmouth
Seniors- Shopping for a Healthy Heart, 2-3 pm, Senior Ctr., South Portland
Taco Cord Holders Teen Craft, 2:15-7 pm, Library, Freeport
Make Art with Art Van (weekly), 3:30 pm, Library, Lewiston
L/A Business Networking, 4-6 pm, DaVinci's Eatery, Lewiston
New to the Region Networking Night, 5-6:30 pm, Leeds
Discover Downtown Westbrook Open House + Art, 5:30 pm, Main St., Westbrook
Mountain Bike Outing, 5:30-7 pm, Neptune Woods, Brunswick
Ukulele Group, 5:30-7 pm, Library, Kennebunk
Waypoints, a Celebration of Portland Trails, 5:30-7 pm, Congress Sq. Park, Portland
Homebuyers Seminar (+ free pizza), 6 pm, Turner St., Auburn
Your Medicare & Social Security Benefits, 6-7:30 pm, High School, Windham
Indigenous Past & Present- Who Tells the Story?, 6-8 pm, Library, Brunswick
Music: Hippie Brothers Band, 6-9 pm, The Axe Pit, South Portland
Author Talk with Rick Simonds, 6:30 pm, Library, North Gorham
Book talk: The History of Coastal Maine, 6:30 pm, Library, South Portland
Music: Adam Swanson, Pianist & Entertainer ($0-10), 6:30-8 pm, Neal St., Portland
Wednesday Warhammer (weekly), 7-11 pm, Croman Game Ctr., Saco
Virtual Events
Learning & Developing Apple Device Skills (Sept 28-Nov 9), 10-11 am
Business Startup Checklist, 1-2 pm
Boat Captain License Info Session, 6-8 pm